paeoniflorigenone

ID: ALA1077668

Cas Number: 80454-42-8

PubChem CID: 133475

Max Phase: Preclinical

Molecular Formula: C17H18O6

Molecular Weight: 318.32

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Paeoniflorigenone | Paeoniflorigenone|80454-42-8|[(1S,3R,6S,8S,10S)-8-hydroxy-3-methyl-5-oxo-2,9-dioxatricyclo[4.3.1.03,8]decan-10-yl]methyl benzoate|CHEMBL1077668|DTXSID201001249|BDBM50378697|(3a-Hydroxy-7a-methyl-6-oxohexahydro-2H-2,5-methano-1,3-benzodioxol-8-yl)methyl benzoate|2,5-Methano-1,3-benzodioxol-6(3aH)-one, 8-((benzoyloxy)methyl)tetrahydro-3a-hydroxy-7a-methyl-, (2S-(2alpha,3abeta,5alpha,7abeta,8R*))-

Canonical SMILES:  C[C@@]12CC(=O)[C@H]3C[C@]1(O)O[C@H](O2)[C@@H]3COC(=O)c1ccccc1

Standard InChI:  InChI=1S/C17H18O6/c1-16-8-13(18)11-7-17(16,20)23-15(22-16)12(11)9-21-14(19)10-5-3-2-4-6-10/h2-6,11-12,15,20H,7-9H2,1H3/t11-,12+,15-,16+,17-/m0/s1

Standard InChI Key:  BANPEMKDTXIFRE-GMKCAIKYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    5.8210  -12.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5423  -12.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5188  -10.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8057  -11.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1116  -12.4453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2401  -11.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2525  -11.9987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0348  -12.2397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5058  -11.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0145  -10.9155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8369  -11.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2132  -10.3556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3308  -11.5514    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2775  -12.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6899  -13.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2711  -13.6228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8829  -14.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1290  -14.2562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2486  -14.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8576  -15.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2225  -16.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9773  -16.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3655  -15.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9982  -14.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9944  -11.0094    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0
  6 12  1  1
  6  7  1  0
  9 13  1  1
  1  2  1  0
  7 14  1  1
  1  4  1  0
 11 15  1  6
  2  7  1  0
 15 16  1  0
  6  3  1  0
 16 17  1  0
  3  4  1  0
 17 18  2  0
  7  8  1  0
 17 19  1  0
  8  9  1  0
 19 20  2  0
  9 10  1  0
 20 21  1  0
 10  6  1  0
 21 22  2  0
 22 23  1  0
  9 11  1  0
 23 24  2  0
 24 19  1  0
 11  4  1  0
  4 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1077668

   PAEONIFLORIGENONE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 318.32

Molecular Weight (Monoisotopic): 318.1103

AlogP: 1.27

#Rotatable Bonds: 3

Polar Surface Area: 82.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.89

CX Basic pKa: ┄

CX LogP: 2.13

CX LogD: 2.12

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.85

Np Likeness Score: 1.89

References

1. Duan WJ, Yang JY, Chen LX, Zhang LJ, Jiang ZH, Cai XD, Zhang X, Qiu F..  (2009)  Monoterpenes from Paeonia albiflora and their inhibitory activity on nitric oxide production by lipopolysaccharide-activated microglia.,  72  (9): [PMID:19691309] [10.1021/np9001898]

2. Ha do T, Ngoc TM, Lee I, Lee YM, Kim JS, Jung H, Lee S, Na M, Bae K..  (2009)  Inhibitors of aldose reductase and formation of advanced glycation end-products in moutan cortex (Paeonia suffruticosa).,  72  (8): [PMID:19670875] [10.1021/np9002004]

3. Mencherini T, Picerno P, Festa M, Russo P, Capasso A, Aquino R..  (2011)  Triterpenoid constituents from the roots of Paeonia rockii ssp. rockii.,  74  (10): [PMID:21954959] [10.1021/np200359v]

4. Ding L, Zhao F, Chen L, Jiang Z, Liu Y, Li Z, Qiu F, Yao X..  (2012)  New monoterpene glycosides from Paeonia suffruticosa Andrews and their inhibition on NO production in LPS-induced RAW 264.7 cells.,  22  (23): [PMID:23067550] [10.1016/j.bmcl.2012.09.034]

Source

Source(1):

• Scientific Literature